4-Bromoaniline → 4-N-(4-bromophenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 2287703Notes

Reaction equation

[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](SC)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:19][C:18]3[CH:20]=[CH:21][C:15]([Br:14])=[CH:16][CH:17]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 78074-Bromoaniline

HCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 53280564-N-(4-bromophenyl)pyrido[4,3-d]pyrimidine-4,7-diamineYield 46.5%

Conditions

Temperature: 200 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (261 mg, 1.36 mmole) and 4-bromoaniline (1.00 g, 5.81 mmole) is stirred under N2 at 200° C. for 15 min. The resulting product is chromatographed on silica gel (10-15% EtOH/EtOAc) to give 7-amino-4-(4-bromoanilino)pyrido[4,3-d]pyrimidine (200 mg, 46%) as a pale yellow solid. 1H NMR (DMSO) δ 9.88 (1H, brs), 9.34 (1H, s), 8.40 (1H, s), 7.83 (2H, d, J=8.8 Hz, 7.55 (2H, d, J=8.8 Hz), 6.64 (2H, brs), 6.44 (1H, s).

Workup

customThe resulting product is chromatographed on silica gel (10-15% EtOH/EtOAc)

Sources & evidence

ORD record: ord-771cf5438f5349f3b43b968f18b327b6
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06084095

Reaction notes

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